Daisy Winfrey

Hyped for Art

Written by Brett Levine

Photo by Jerry Siegel

For illustrator Daisy Winfrey, the road to art wasn’t without its detours. “I came back to art when I was almost 30 after a career that had involved working in an insurance office and had even started when I made the decision not to study fashion,” she explains. But what separates Winfrey from many other artists, but in many ways unites her with many of her peers, is her understanding of the principle of how she can make a living from her work. “I had someone say something to me once that really transformed the way I thought about my work. She said, ‘You should learn to let your merchandise support your art.’ What she meant by that was that there was a way to produce a range of pieces that would reach people at a variety of price points and in a number of ways–and that there was nothing wrong with that,” she says. This led to some of Winfrey’s most humorous, engaging, and accessible work, including a series of hip-hop-inspired postcards in packets of 10, on which 1950s-style Dick-and-Jane-style children remark, “Chuck D. was RIGHT. I should NEVER have believed all that hype.” “What amazes me,” Winfrey says, “is that people are so amazed when they realize that the 10 cards in the pack are all different!”.

“I’m obsessed with acrylic ink,” she says, “in part because it is so versatile. It allows me to get the color of oil paint without the drying time.” This sense of urgency is something that is almost palpable. Winfrey’s home is filled with works in progress to the extent that there is a studio workspace in one room and a separate drawing table set up in the living room. “I feel like I need to constantly be working,” she says with a smile. “I have the sense that if I’m not doing something creative it is almost as if I am wasting my time.”

In addition to the postcards, Winfrey makes large-scale portraits, intricately handmade, sewn, and embroidered garments, and other works that explore the ideas of history, identity, and significance. “I did a series early in my career where I drew on paper bags. I wanted to challenge the idea of material value—literally, the idea of working on an art material—and I also wanted to question how these works might hold up for the future. I called those my Future Myths.”

Winfrey always works in series. “I never make one piece by itself. I prefer to think how a whole series of works will work together.” Her desire to work with many different (and accessible) materials presents its own challenges, however. “I think one of the biggest misunderstandings people have about my work is that I’m not a folk artist,” she says. “I might be influenced by early Americana, or a style of portraits that share hard outlines, but just because my work is not highly polished, people make the mistake of calling it ‘folk.’ It is actually an outcome of my materials,” she continues. “Working with gouache, encaustic, collage, and paper—diverse materials—lends itself to a look that makes me think of memories, but many people simply characterize this style of work as naïve or unfinished.”

One of her other challenges is simply being willing to let go. “Sometimes I work on something a long time, and then in the process of finding what I want the work to say, I end up covering over the intricacies of the details.” Pointing at a large work in progress hanging on the studio wall she explains, “What you can’t really see now is all the text that is actually painted underneath her clothes.”

One of the great indicators of complex work is its ability to continue to challenge viewers after their initial encounter, its ability to draw them in, to make them look, to hold them just a moment longer. Winfrey has that ability. Sure, much of her work is characterized by humor, by her unabashed love of hip-hop and pop culture, and that is what allows her to engage so quickly with such a large audience. But on a deeper level, in her more subtle works, she invites viewers to share her memories, to experience her histories, and to see her vision. She is, quite simply, telling stories she hopes will be significant in the future.